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Carboxylic Acids to Methylesters: Alkylation using Diazomethane

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The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.

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Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:

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Ethyl anthracene-9-carboxyl-ate.

Edwin Weber, Wilhelm Seichter, Conrad Fischer

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This summary is machine-generated.

This study details the crystal structure of a novel organic compound, C(17)H(14)O(2). Key findings include specific dihedral and torsion angles, and stabilization through intermolecular interactions like C-H⋯O bonds.

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Area of Science:

Crystallography
Organic Chemistry
Supramolecular Chemistry

Background:

Understanding molecular interactions is crucial in crystal engineering.
Anthracene derivatives are widely studied for their unique electronic and structural properties.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(17)H(14)O(2).
To analyze the molecular conformation and intermolecular forces governing crystal packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
Analysis of bond angles, torsion angles, and non-covalent interactions (C-H⋯O and arene interactions).

Main Results:

The COO group and anthracene fragment exhibit a dihedral angle of 76.00(19)°.
The ester group's O-Csp(3) bond has a torsion angle of 108.52(18)°.
Crystal structure is stabilized by C-H⋯O interactions and edge-to-face arene interactions (2.75–2.84 Å).

Conclusions:

The study provides detailed structural information on C(17)H(14)O(2).
Identified intermolecular interactions offer insights into crystal packing and design principles for related organic materials.